When picking presidents, for some reason business failure works more charms with American voters than financial success. Thomas Jefferson, Theodore Roosevelt, Ulysses S. Grant and Harry S. Truman were among those presidents who made a mess of their business affairs. Not that it held any of them back from serving more than one term.

No candidate, however, has done what GOP presidential nominee Mitt Romney is attempting: Get elected president on the strength (or despite the liabilities) of his income statement.

One reason the U.S. has elected few presidents who were successful in business is that, some in the U.S. electorate might imagine, a financial dealmaker in the White House might only go there to corner the wheat market or perhaps service an oligopoly.

Though a handful of the early Virginia planter presidents ran their family estates, most candidates have been drawn from the narrow circles of the law and the military — as opposed to the membership of the Union League Club in New York.

In the 20th century, only Herbert Hoover made big money in business before becoming president — though he had served eight years in the Cabinets of Presidents Warren Harding and Calvin Coolidge before seeking office.

It is true that both George H.W. Bush and George W. Bush worked in business before becoming president. But their claims to power came from their political dynasty, not their wealth.

To many U.S. voters, a successful businessman may well have cut corners, doled out bribes or fiddled with the books. The accepted template for presidents, however, is that they must be mythical men with a homespun past — as George Washington was, or as Ronald Reagan became, when he walked from his Iowa lifeguard stand to the White House.

Nonetheless, as a businessman, Washington used all the tricks that Romney would have known at Bain. He worked his fields with slaves, padded his revolutionary expense accounts and used his governmental appointments to buy up tracks of land at discounted prices. These actions were forgotten over the long course of the Revolution.

Though Romney served one term as governor of Massachusetts, his defining career has been in business. He also managed the Salt Lake City Olympic Games, but selling box seats and TV rights hardly counts as public service.

Romney’s buyout firm, Bain, leveraged the partners’ capital with those of outside investors to buy, reorganize, create, shut down, merge and sell companies — some of which flourished, like Staples, others of which went belly up.

As portrayed in President Barack Obama’s campaign ads, Bain has now become synonymous for ruthlessness with E.H. Harriman’s Union Pacific Railroad, if not Andrew Carnegie’s U.S. Steel. As a venture capital firm in the 1980s and 90s, however, Bain was little different from thousands of other such companies and funds — except it was more successful.

The paradox of Romney is that he seems to combine the weaknesses of both the plutocratic and political classes. As an executive, he is described as being secretive, controlling and hierarchical. As a politician he changes his mind often, something titans are not supposed to do. Why vote for a robber baron if he sounds like George Babbitt?

Qualities that lead to business success — the love of monopoly in John D. Rockefeller, for example, or the killer marketing instinct in Bill Gates — are rarely sought in U.S. politicians, many of whom might seem to have been selected because they were mediocre and threatened few interests.

The republic has turned away a number of presidential candidates — precisely because they looked a little too accomplished at making money. Consider Ross Perot or even Donald Trump. In the Revolutionary period, it was the financier and millionaire trader Robert Morris who got nowhere in his hope of being another Founding Father who later became president.

Unlike the personal fortunes of, say, Hillary and Bill Clinton or Lyndon B. Johnson, Romney did not make his money as a fringe benefit of his political fame — another reason his business past may be suspect. The fortunes of recent presidential candidates sometimes look a bit like lottery winnings.

The Clintons, after primarily working in government jobs for more than 30 years, have a net worth now estimated at $85 million. Texas political operatives allegedly handed George W. Bush part of his $15 million fortune while buying the local baseball team.

Yet it is Romney who raises suspicion for, among other things, withholding his tax returns, paying 13 percent federal income taxes, surreptitiously controlling Bain from 1999 to 2002 and investing in funds based in the Cayman Islands. He looks a little too fond of his money.

Americans have no problem electing multimillionaires to the presidency, provided they didn’t make the money themselves. Franklin D. Roosevelt, his cousin Teddy Roosevelt, and John F. Kennedy are among those who were worth millions (in today’s dollars) in the White House, but whose ancestors earned the fortunes. In the case of FDR, his grandfather traded opium in China. Kennedy’s father “imported” liquor.

Had Romney run for office during the go-go years of the 1990s, his fortune might have been a footnote to the campaign. Who in 2004 begrudged Sen. John Kerry a marriage dowry of $250 million? It was wind surfing that capsized his campaign.

In this prolonged economic slump, however, Romney can be sketched along Thomas Nast fat-cat lines, for whom the presidency is another executive perk.

To understand why businessmen fare so poorly as presidential candidates, look how they are portrayed in American literature. Leaving aside the empathetic character of Silas Lapham in the William Dean Howells novel, most writers cast their dealmakers as villains, the last man you would want in a smoke-filled room deciding the fate of your Medicare payments.

For example, Theodore Dreiser’s Frank Cowperwood, F. Scott Fitzgerald’s Jay Gatsby, and Frank Norris’s S. Behrman use their considerable skills and charms to bootleg liquor or monopolize the railways — not to reform Social Security or repay bondholders.

What serious author would write a novel about a successful hedge fund manager who becomes a terrific president?

Matthew Stevenson, a contributing editor to Harper’s Magazine, is the author of “Remembering the 20th-Century Limited,” a collection of historical travel essays. His next book is “Whistle-Stopping America.”